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How to meet women through online dating and not get caught by your wife

April 14, 2012

This is a guide for a married man who would like to develop an intimate relationship with someone besides his wife. There are several guides out there for online dating: what to look like, what to say, who to contact, etc., but I have yet to find one that makes exceptions for men (or women) who would like to remain anonymous online while attempting to meet people. Without further ado, here is a list of guidelines I have developed for married men interested in meeting others online (for sex, debate, walks, or cribbage):

1. Do not post a picture of yourself that is easily identifiable.

This rule is obvious, but all guides for online dating state just the opposite. Yes, most people that browse dating sites use your picture as an initial weeding out factor. “Is he cute? Ok! I’ll respond to his email.” Unless you have an open marriage, however, do not post your picture online. You will send them your picture later. (More on this below.)

2. Forget about women that are only looking for single men. 

Most women on online dating sites are single and looking for men that are single. They are typically not interested in married men. But there are some women that are willing to have relationships with married men. These women either believe that the man is physically or emotionally separated from his wife or don’t care.

3.  Do not make your first contact sound like you are a predator.

Trying to get laid is OK, but it takes finesse unless you are planning on doping your date’s drink and dragging her into the woods. Women are smart these days. They are aware of predators and avoid them. Find something interesting about her profile and talk about that. If she takes a look at your profile and responds you have reached level 2 (The one percent club).

4. Do not follow-up immediately.

You are married. Chances are you have a job. You may even have kids and other extra-curricular activities besides lurking on an internet dating site. Portray yourself as someone who can take it or leave it–women love that. They want to be pursued, but only by someone that is generally not a pursuer, like a stalker or someone who is desperate. You must wait at least 24 hours before sending a second message to a women after she has replied to your initial message. If she does not ask any questions in her response, you must wait three business days. Trust me, this is important.

5. Do not send your picture until she asks for it.

It’s the same rule that you follow when you go to a job fair: never give out your finely crafted resume to someone who isn’t interested. Send at least three messages to her (including the initial one) that are thoughtful, inquisitive, and on-point. Humor also helps. Eventually, if she is interested in meeting you, she will ask for your picture. Then you can send her one.

6. See if she is still interested before proposing a meeting.

She’s seen your picture. She was probably disappointed. What happens is that she pictured you as having certain features that she is willing to accept. Once she actually sees you, some of those visions are broken. It may take her some time to come around. On the other hand, she may think you are cute. She will respond and continue on the conversation. That’s your cue to ask her for a date.

7. Make your first date very low-key.

You’ve made it this far. You are in the realm of the rare. A married man has met a woman online with the hopes of having some kind of emotional and/or physical relationship and she agreed to meet him somewhere. Good places for this first encounter are public and highly visible. A coffee shop is a good choice, preferably one in which neither of you are regulars. Have fun. Have an interesting, lighthearted conversation. Politics, religion, and ethics are poor choices for topics. Stay for an hour at most. Again, you have a life. Don’t invite her to your apartment or for a ride. Think of something fun to do for your next date ahead of time and ask her if she is interested. If not, wait for her to propose something.

That’s it. You’ve successfully navigated the course. Good luck.

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